An Elite Executive's Observations on my Last Blog Post about the Overbearing CTO

This is one of those posts where the observations and insights from my reading audience takes front and center. I have the very good fortune of knowing a truly amazing technology executive that reads my blog on a pretty regular basis. His career has been incredible and while he is currently enjoying some time off after a very successful stint of a startup CTO, he does everything he can to stay in the trenches and embedded in Austin's technology ecosystem. In response to my last post about the overbearing CTO, he reached out to me with his thoughts on the matter. This post will primarily focus on the words of this executive and I'll also do my best to share my thoughts as well. Let's cut to the chase and I'll paste his first words for you here,?

Most engineers view the CTO role as nirvana, but one thing often missed: At the end of the day, it’s still a kind of middle management. The culture is set by the CEO (and the investors pressuring the CEO) and as a manager there is always a need to balance the pressure one is getting from above with how much to buffer it from your directs. Buffer too much and your manager is on your case, and the team is probably not performing as well as they could. Buffer too little and the team resents you (and, again, they’re probably not as effective as they could be). It’s really difficult to get this just right!

Whether it be a professional or even a personal setting, as we all very well know, balancing acts and appeasing all parties can be very difficult to do. So the CTO in my previous story very well could have been struggling with that balance. And perhaps the critical moment arrived where the team's software deliverable did not meet his expectations and a result, he lost it and emotionally exploded on his team.? And again, this was a Fintech startup and that space currently is under a lot of pressure so the words above from this executive very well could have been in play.?

From here, this executive offered some more words and this time, it had to do with the CEO/President of the company.?

Was thinking more about this. The CEOs I’ve met often privately wonder why the entire product backlog can’t be done today. I’ve had conversations where I’ve been asked “why are we prioritizing components of the engineering work? It’s all highest priority.” I’ve actually had to explain that we can’t do everything at once and we need prioritization to know what to work on next. This isn’t one place, it’s par for the course at the executive level in my experience.

One of the most important things a CTO can do for a company is bring some perspective to the executive team of someone who has actually done some significant engineering. Of course the trick is to maintain empathy for both the engineers and the executive team. Ideally, I think we want to build timely quality technology that gives a great return to the investors, while also providing fulfilling work to the employees with strong compensation and significant growth opportunities. It’s rare that all these things are balanced perfectly.

What I like about these words above is that it sounds like there are moments in a CTO's career when he/she has to educate other members of the executive team. Especially with technology startups, isn't everything hinging on the engineering team to deliver?? And if that is the case, in terms of creating the "buffer" that is spoken about earlier in the post, does the CEO, to a degree, have to be educated on timelines and expectations? And who better to do that than the CTO, especially one who came up in their career as a programming heavy software engineer.?

But again, the executive who shared these words with me returns to the very delicate balance of appeasing multiple parties, ie. making sure the investors are satisfied, along with the other executives while at the same time providing a healthy and productive workplace environment for the engineering team. And I'm here to say that right now in these current labor markets, the tables very much seem to be titled towards the best interests of the investors. Even though the number of layoffs has ebbed recently, the vast majority of phone calls I'm having today with software engineers looking for new jobs are because of the incredible amounts of pressure and stress they are enduring on a daily basis. And they are approaching the moment where they can no longer take it anymore.? ?

While this is no easy task at all, if you are in the late stages of interviewing with a company, upon meeting the company's VP of Engineering or CTO, could you try to determine how much of an advocate they would be for the engineering organization? I'll say it again that in these currently high stress labor markets, sentiment is heavily on the side of the investors and the expectations are 100% on the engineering team to deliver in perfect fashion. But perhaps you could explore the background of the CTO and whether they came up as a software engineer like you have in your career? And if so, how much of an advocate would they be for you and your team? Make no mistake, this would not be an easy task but perhaps in your 45-60 minute conversation, you could gain a little insight into what kind of CTO/VP you'd be working for??

In closing, I thanked this executive immensely for these words and while he's done very well in his career, he is still very much staying in the trenches and whenever the right opportunity comes open again, he's ready to jump back into the game. But right now, life if treating him really well and he finished his commentary with the following words,?

Make no mistake, I have definitely had my moments of frustration with the engineering teams I have led but cursing out the team publicly and dropping a bunch of F-bombs like you describe is unprofessional and unproductive. You just cannot let yourself go that far down the hole.

And once again, I agreed 100% with him and thanked him greatly...

Thanks,?

Mark Cunningham

Technical Recruiter

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